Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-β-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.
Chemoenzymatic synthesis and antitumor promoting activity of 6 '- and 3-esters of 2-O-beta-D-glucosylglycerol / D. Colombo, F. Compostella, F. Ronchetti, A. Scala, L. Toma, H. Tokuda, H. Nishino. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 7:9(1999), pp. 1867-1871. [10.1016/S0968-0896(99)00137-6]
Chemoenzymatic synthesis and antitumor promoting activity of 6 '- and 3-esters of 2-O-beta-D-glucosylglycerol
D. ColomboPrimo
;F. CompostellaSecondo
;F. Ronchetti;A. Scala;
1999
Abstract
Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-β-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.
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